Cycloserine
Created:
9/30/19
Submitted:
10/8/26
Published:
10/8/26
6234-bas-color-print_cautionAtoms shown as ball-and-stick (geometry appears faceted on screen; apply smooth normals in Blender or similar to improve visualization; generally smooth when 3D printed) with standard colors. 3D printable, with caution, using certain 3D printers.
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Description
D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanineD-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). It has a role as a metabolite, an antitubercular agent, an antimetabolite, an antiinfective agent and a NMDA receptor agonist. It is a 4-amino-1,2-oxazolidin-3-one, an organonitrogen heterocyclic antibiotic and an organooxygen heterocyclic antibiotic. It is a conjugate base of a D-cycloserine(1+). It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion.
